e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

Polycyclic hydroxyquinones. 13. A novel synthesis of islandicin and digitopurpone

P Cano, A Echavarren, P Prados…

Index: Cano, Pilar; Echavarren, Antonio; Prados, Pilar Journal of Organic Chemistry, 1983 , vol. 48, # 26 p. 5373 - 5376

Full Text: HTML

Citation Number: 15

Abstract

Recent interest in anthracyclines2 is due to the useful antitumor activity which they possess and has stimulated the development of new routes to related systems and regiospecific synthesis of unsymmetrically substituted anthraquinones, which could be used as intermediates or synthetic models for anthracyclinones. The use of 3-hydroxy-2-pyrone (1) as a diene in the Diels-Alder reaction, reported by Corey et al., 3 could be

N/A Structure

Ethanoic anhydride Structure

Ethanoic anhydride

~94%

(4-acetyloxy-3-chloro-6-methyl-5,8-dioxonaphthalen-1-yl) acetate Structure

(4-acetyloxy-3-...

Learn More

3-Hydroxy-2H-Pyran-2-One Structure

3-Hydroxy-2H-Py...

(4-acetyloxy-3-chloro-6-methyl-5,8-dioxonaphthalen-1-yl) acetate Structure

(4-acetyloxy-3-...

~50%

(4-acetyloxy-5-hydroxy-3-methyl-9,10-dioxoanthracen-1-yl) acetate Structure

(4-acetyloxy-5-...

Learn More

N/A Structure

~%

(4-acetyloxy-5-hydroxy-3-methyl-9,10-dioxoanthracen-1-yl) acetate Structure

(4-acetyloxy-5-...

Learn More

3-Hydroxy-2H-Pyran-2-One Structure

3-Hydroxy-2H-Py...

N/A Structure

~16%

Digitopurpone Structure

Learn More

3-Hydroxy-2H-Pyran-2-One Structure

3-Hydroxy-2H-Py...

1,4-Naphthalenedione,5,8-bis(acetyloxy) Structure

1,4-Naphthalene...

~50%

(4-acetyloxy-5-hydroxy-9,10-dioxoanthracen-1-yl) acetate Structure

(4-acetyloxy-5-...

Learn More

3-Hydroxy-2H-Pyran-2-One Structure

3-Hydroxy-2H-Py...

(4-acetyloxy-6-chloro-5,8-dioxonaphthalen-1-yl) acetate Structure

(4-acetyloxy-6-...

~13%

(4-acetyloxy-5-hydroxy-9,10-dioxoanthracen-1-yl) acetate Structure

(4-acetyloxy-5-...

(4-acetyloxy-3-chloro-5-hydroxy-9,10-dioxoanthracen-1-yl) acetate Structure

(4-acetyloxy-3-...

Detail Learn More

3-Hydroxy-2H-Pyran-2-One Structure

3-Hydroxy-2H-Py...

(4-acetyloxy-3-chloro-5,8-dioxonaphthalen-1-yl) acetate Structure

(4-acetyloxy-3-...

~13%

(4-acetyloxy-5-hydroxy-9,10-dioxoanthracen-1-yl) acetate Structure

(4-acetyloxy-5-...

(4-acetyloxy-3-chloro-5-hydroxy-9,10-dioxoanthracen-1-yl) acetate Structure

(4-acetyloxy-3-...

Detail Learn More

3-Hydroxy-2H-Pyran-2-One Structure

3-Hydroxy-2H-Py...

6-chloro-2-methylnaphthazarin Structure

6-chloro-2-meth...

~20%

9,10-Anthracenedione,1,4,5-trihydroxy-2-methyl Structure

9,10-Anthracene...

Learn More

3-Hydroxy-2H-Pyran-2-One Structure

3-Hydroxy-2H-Py...

Naphthazarin Structure

~26%

9,10-Anthracenedione,1,4,5-trihydroxy Structure

9,10-Anthracene...

Learn More

3-Hydroxy-2H-Pyran-2-One Structure

3-Hydroxy-2H-Py...

Naphthazarin Structure

~7%

5,8-dihydroxy-2,3-dihydronaphthalene-1,4-dione Structure

5,8-dihydroxy-2...

9,10-Anthracenedione,1,4,5-trihydroxy Structure

9,10-Anthracene...

Learn More

5,8-dihydroxy-2,3-dihydronaphthalene-1,4-dione Structure

5,8-dihydroxy-2...

Ethanoic anhydride Structure

Ethanoic anhydride

~97%

(4,5,8-triacetyloxynaphthalen-1-yl) acetate Structure

(4,5,8-triacety...

Learn More

Naphthazarin Structure

~%

(4,5,8-triacetyloxynaphthalen-1-yl) acetate Structure

(4,5,8-triacety...

Learn More

3-Hydroxy-2H-Pyran-2-One Structure

3-Hydroxy-2H-Py...

(4-acetyloxy-6-chloro-5,8-dioxonaphthalen-1-yl) acetate Structure

(4-acetyloxy-6-...

~0%

(4-acetyloxy-5-hydroxy-9,10-dioxoanthracen-1-yl) acetate Structure

(4-acetyloxy-5-...

(4-acetyloxy-3-chloro-5-hydroxy-9,10-dioxoanthracen-1-yl) acetate Structure

(4-acetyloxy-3-...

Detail Learn More

3-Hydroxy-2H-Pyran-2-One Structure

3-Hydroxy-2H-Py...

Naphthazarin Structure

~6%

5,8-dihydroxy-2,3-dihydronaphthalene-1,4-dione Structure

5,8-dihydroxy-2...

9,10-Anthracenedione,1,4,5-trihydroxy Structure

9,10-Anthracene...

Learn More

3-Hydroxy-2H-Pyran-2-One Structure

3-Hydroxy-2H-Py...

(4-acetyloxy-3-chloro-5,8-dioxonaphthalen-1-yl) acetate Structure

(4-acetyloxy-3-...

~0%

(4-acetyloxy-5-hydroxy-9,10-dioxoanthracen-1-yl) acetate Structure

(4-acetyloxy-5-...

(4-acetyloxy-3-chloro-5-hydroxy-9,10-dioxoanthracen-1-yl) acetate Structure

(4-acetyloxy-3-...

Detail Learn More

3-Hydroxy-2H-Pyran-2-One Structure

3-Hydroxy-2H-Py...

(4-acetyloxy-6-chloro-5,8-dioxonaphthalen-1-yl) acetate Structure

(4-acetyloxy-6-...

~0%

(4-acetyloxy-5-hydroxy-9,10-dioxoanthracen-1-yl) acetate Structure

(4-acetyloxy-5-...

(4-acetyloxy-3-chloro-5-hydroxy-9,10-dioxoanthracen-1-yl) acetate Structure

(4-acetyloxy-3-...

Detail Learn More

3-Hydroxy-2H-Pyran-2-One Structure

3-Hydroxy-2H-Py...

(4-acetyloxy-3-chloro-5,8-dioxonaphthalen-1-yl) acetate Structure

(4-acetyloxy-3-...

~0%

(4-acetyloxy-5-hydroxy-9,10-dioxoanthracen-1-yl) acetate Structure

(4-acetyloxy-5-...

(4-acetyloxy-3-chloro-5-hydroxy-9,10-dioxoanthracen-1-yl) acetate Structure

(4-acetyloxy-3-...

Detail Learn More